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Record Information
Version4.0
Creation Date2013-07-22 19:49:31 UTC
Update Date2017-09-27 08:44:02 UTC
HMDB IDHMDB0061126
Secondary Accession Numbers
  • HMDB61126
Metabolite Identification
Common Name4,5-Dihydro-drospirenone-3-sulfate
Description4,5-Dihydro-drospirenone-3-sulfate is a metabolite of drospirenone. Drospirenone, also known as 1,2-dihydrospirorenone, is synthetic, steroidal progestin with additional antimineralocorticoid and weak antiandrogen properties which is used as a hormonal contraceptive. It is sold under the brand names Yasmin, Yasminelle, Yaz, Beyaz, Ocella, and Angeliq, all of which are combination products of drospirenone with an estrogen such as ethinylestradiol. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H34O5S
Average Molecular Weight434.589
Monoisotopic Molecular Weight434.212694888
IUPAC Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
Traditional Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O1
InChI Identifier
InChI=1S/C24H34O5S/c1-22-6-3-12(30(26,27)28)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(25)29-24/h12-18,20-21H,3-11H2,1-2H3,(H,26,27,28)/t12?,13-,14+,15-,16?,17?,18+,20?,21?,22-,23+,24?/m1/s1
InChI KeyZHIWICDXDMTIEM-AAQOLUSRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassLactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Tetrahydrofuran
  • Alkanesulfonic acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP1.12ALOGPS
logP3.07ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)-0.73ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity110.4 m³·mol⁻¹ChemAxon
Polarizability47.7 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cdj-0039200000-621e05258d19f492d39dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1007900000-6856048d0c9d173a1f91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h6r-0039100000-cbad5ebfff23c24d2d29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2190000000-70973bb507f87249d9d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1002900000-e95169f4809e9a97882dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2007900000-b41f8677923743b00108View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9001000000-f975c52679d9f108c58dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00741
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available